Literature DB >> 23270309

Enantioselective total synthesis of hyperforin.

Brian A Sparling1, David C Moebius, Matthew D Shair.   

Abstract

A modular, 18-step total synthesis of hyperforin is described. The natural product was quickly accessed using latent symmetry elements, whereby a group-selective, Lewis acid-catalyzed epoxide-opening cascade cyclization was used to furnish the bicyclo[3.3.1]nonane core and set two key quaternary stereocenters.

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Year:  2012        PMID: 23270309     DOI: 10.1021/ja312150d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

1.  Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Authors:  Mikayo Hayashi; Lauren E Brown; John A Porco
Journal:  European J Org Chem       Date:  2016-10

Review 2.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

3.  The first total synthesis and the second- or third-generation approach.

Authors:  Keiichi Ajito
Journal:  J Antibiot (Tokyo)       Date:  2016-04       Impact factor: 2.649

4.  Local Desymmetrization through Diastereotopic Group Selection: An Enabling Strategy for Natural Product Synthesis.

Authors:  Matthew A Horwitz; Jeffrey S Johnson
Journal:  European J Org Chem       Date:  2017-02-07

5.  Enantioselective Total Synthesis of Nigelladine A via Late-Stage C-H Oxidation Enabled by an Engineered P450 Enzyme.

Authors:  Steven A Loskot; David K Romney; Frances H Arnold; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2017-07-24       Impact factor: 15.419

6.  Total Synthesis and Anticancer Activity of (+)-Hypercalin C and Congeners.

Authors:  Yongfeng Tao; Keighley Reisenauer; Joseph H Taube; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-01       Impact factor: 15.336

7.  Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization.

Authors:  Jonathan H Boyce; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-10       Impact factor: 15.336

8.  A Scalable Protocol for the Regioselective Alkylation of 2-Methylcyclohexane-1,3-dione with Unactivated sp3 Electrophiles.

Authors:  Robert J Sharpe; Maribel Portillo; Robert A Vélez; Jeffrey S Johnson
Journal:  Synlett       Date:  2015-08-21       Impact factor: 2.454

Review 9.  Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.

Authors:  Martin Büschleb; Stéphane Dorich; Stephen Hanessian; Daniel Tao; Kyle B Schenthal; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

10.  Synthesis of medicinally relevant terpenes: reducing the cost and time of drug discovery.

Authors:  Daniel J Jansen; Ryan A Shenvi
Journal:  Future Med Chem       Date:  2014-06       Impact factor: 3.808

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